Coclaurine

Coclaurine
Names

Preferred IUPAC name (1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
CAS Number	486-39-5^Y
3D model (JSmol)	Interactive image
ChemSpider	141028
KEGG	C06161^Y
PubChem CID	160487
UNII	CW1576313Y^Y
CompTox Dashboard (EPA)	DTXSID60197561
InChI InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1 Key: LVVKXRQZSRUVPY-HNNXBMFYSA-N InChI=1/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1 Key: LVVKXRQZSRUVPY-HNNXBMFYBJ
SMILES COC1=C(C=C2[C@@H](NCCC2=C1)CC3=CC=C(C=C3)O)O
Properties
Chemical formula	C₁₇H₁₉NO₃
Molar mass	285.343 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Coclaurine is a nicotinic acetylcholine receptor antagonist^[1] which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum,^[2] Ocotea duckei,^[3] and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.

References

^ https://www.researchgate.net/profile/Matthew_Cheesman4/publication/303689274_Oceania_Antidepressant_Medicinal_Plants/links/5aa85083a6fdcc1b59c63bda/Oceania-Antidepressant-Medicinal-Plants.pdf ^{[bare URL PDF]}
^ Sowemimo BO, Beal JL, Doskotch RW, Svoboda GH (1972). "The isolation of stepharine and coclaurine from Sarcopetalum harveyanum". Lloydia. 35 (1): 90–91. PMID 5037484.
^ I.G da Silva; J.M Barbosa-Filho; M.S da Silva; C.D.G de Lacerda; E.V.L da-Cunha (2002). "Coclaurine from Ocotea duckei". Biochemical Systematics and Ecology. 30 (9): 881–883. Bibcode:2002BioSE..30..881D. doi:10.1016/s0305-1978(02)00024-8.

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists (and PAMsTooltip positive allosteric modulators)	5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083
Antagonists (and NAMsTooltip negative allosteric modulators)	18-MAC 18-MC α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others) ABT-126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates (e.g., pentobarbital, sodium thiopental) BNC-210 Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin) Bupropion BW284C51 BW-A444 Candocuronium iodide (chandonium iodide) Chlorisondamine Cisatracurium Coclaurine Coronaridine Curare Cyclopropane Dacuronium bromide Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine (metocurine) Dioscorine Dipyrandium Dizocilpine (MK-801) Doxacurium Encenicline Enflurane Erythravine Esketamine Fazadinium Gallamine Gantacurium chloride Halothane Hexafluronium Hexamethonium (benzohexonium) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenic acid Laudanosine Laudexium (laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan (racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (racemorphan) Neramexane Nitrous oxide Norketamine Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium bromide Progesterone Promegestone Radafaxine Rapacuronium bromide Reboxetine Rocuronium bromide Sevoflurane Stercuronium iodide Surugatoxin Thiocolchicoside Threohydrobupropion Toxiferine Tramadol Trimetaphan camsilate (trimethaphan camsylate) Tropeinium Tubocurarine Vanoxerine Vecuronium bromide Xenon

Agonists
(and PAMsTooltip positive allosteric modulators)